If you had $100,000 for your boat, refit and add extras if needed, watermaker, Reverse A/C, electronics... for a total of $100,000

Would you buy an older boat in the 37 - 45 foot for less than $50k or so and then replace everything, electronics, sails, rigging, motor rebuild.. that sort of refit

or

Buy a newer boat for much closer to $100k and then just hope most things don't need immediate repair/replacement? like a

Since we are going to be retired I am not overly worried about how fast I get there as am I having fun on the way there.. Comfort and keeping the better half having fun and seeing the world is the goal . So I don't really want to be roughing it too much.

We are looking to retire in a year or so and are really starting the shopping process...

Want to cruise the usual, Caribbean all the way down to South America and then maybe a RTW after a year or two shake down of the boat?

So Newer and less comfort and options or older and really tricked out?

lol, I know not a new boat but newer one.. Say something in the 2000's in the 36 - 40 ft range.. But like you said, even if it fits in my $100k price, it will leave little to nothing to repair/refit/add the bells and whistles...

I think it depends on how much you can do yourself. I had a 30-YO Irwin 31 Citation that was solid, but I was continually working on her. I now have a 2002 Hunter 306 and love the fact that outside of normal maintenance, I don't have to do much and find that I sail a hell of a lot more!

Captainrizzo,
That is exactly what I'm afraid of. While I am very handy and can fix/repair most anything on land and I think I can do almost as well on water, I don't want to spend the first year working so much on the boat that I don't get to enjoy it as much...

May go to Croatia as I have friends over there and buy a newer boat and sail the med for a year and then take ARC back over the following Nov...

I can't tell you what to do, but can tell you what we did ... which was to buy an older boat, sooner, and spend a couple of years learning her inside out, replacing everything so it was exactly the way we wanted it, then sailing away debt free. We got a lot more boat than we could have if we got a newer one, and when anything did go wrong, we knew how to fix it because we were the ones who installed it in the first place. But: we had time (started this work a few years before we were ready to retire) and skills (both engineers, with a former kitchen/bath remodel business). Instead of asking a bunch of strangers on the internet what to do, have you asked your wife what will keep her "happy and having fun?" Newer & smaller or older & bigger, etc?

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I agree with Jaye (wingnwing). Ask your wives/SOs what they want. Go over a list of pros and cons for newer vs. older. Then, ask them for a list no matter how outlandish you may think it is. Work together to discuss why things may or may not be practical and get the list down to something reasonable. Visit boat shows with the list. Board boats for sale with the list even if you have no intention of buying it. Together. It may seem silly and a lot of work now, but in two years if you're enjoying your boat and your SO no longer wants to be bothered, you might think differently.

We did it in reverse. Once we decided where our primary cruising area was going to be TODAY, not ten years from now, I did all the boat research but I did it with a list in hand of Must Haves from John. Well, there were only two items on his list since it was his first boat (my second). Three if you count No Project Boat (that was my first boat).

We went to a couple boat shows. We sat in the cabins while people streamed past us to see how comfortable a particular boat was.

Then I narrowed it down to three different boats and presented a list of pros and cons for each. We chose one together, I told him when to show up for the sea trial and who to make the check out to and BAM! Done. And men say women make things more complicated than they need to be.

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